Issue 3, 2017

Pentafluorobenzene end-group as a versatile handle for para fluoro “click” functionalization of polythiophenes

Abstract

A convenient method of introducing pentafluorobenzene (PFB) as a single end-group in polythiophene derivatives is reported via in situ quenching of the polymerization. We demonstrate that the PFB-group is a particularly useful end-group due to its ability to undergo fast nucleophilic aromatic substitutions. Using this molecular handle, we are able to quantitatively tether a variety of common nucleophiles to the polythiophene backbone. The mild conditions required for the reaction allows sensitive functional moieties, such as biotin or a cross-linkable trimethoxysilane, to be introduced as end-groups. The high yield enabled the formation of a diblock rod-coil polymer from equimolar reactants under transition metal-free conditions at room temperature. We further demonstrate that water soluble polythiophenes end-capped with PFB can be prepared via the hydrolysis of an ester precursor, and that such polymers are amenable to functionalization under aqueous conditions.

Graphical abstract: Pentafluorobenzene end-group as a versatile handle for para fluoro “click” functionalization of polythiophenes

Supplementary files

Article information

Article type
Edge Article
Submitted
04 oct. 2016
Accepted
06 dic. 2016
First published
15 dic. 2016
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2017,8, 2215-2225

Pentafluorobenzene end-group as a versatile handle for para fluoro “click” functionalization of polythiophenes

P. Boufflet, A. Casey, Y. Xia, P. N. Stavrinou and M. Heeney, Chem. Sci., 2017, 8, 2215 DOI: 10.1039/C6SC04427A

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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